1983
DOI: 10.1021/jo00159a024
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Copper(I)-catalyzed coupling reaction between phenylmagnesium bromide and 3,3,3-trifluoropropene

Abstract: brucination cycle applied to the +90.2°material gave 900 mg of volatiles (a^+68.9°) and from the brucine 340 mg (am +122.1°) of volatiles. A gas chromatographic analysis of this last fraction gave 95.3% 2,3-dibromobutane, 2.5% 2-bromo-2-butene, 0.6% diethyl ether, and 1.5% CFC13. Differential scanning calorimetry applied to this best fraction indicated the dextrorotatory component was 70% of this mixture, the remainder being d,l and the other listed contaminants.Registry No. (fi*,f?*)-(±)-2,3-Dibromobutane, 59… Show more

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Cited by 22 publications
(1 citation statement)
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“…21. In the case of compounds of type 30 with X ϶ H, the influence of X and the phenyl group at C-1 on the chemical shift of the 3-H signal is not as straightforward as might appear considering the compounds in Table 1. Thus, the configurations of compounds 30 cannot easily be correlated with the δ values of 3-H, as shown, for example, by considering the data for 30a with X ϭ Me, [46] X ϭ F, [47] X ϭ Scheme 6. NOE enhancements observed for the 1 H NMR signals Cl, [48] and X ϭ Br [49] or 30b with X ϭ Me, [50] X ϭ Bu, [9] of (E)-3 and results derived from 1 H NMR spectra of 4t and 26t X ϭ CH 2 Ph, [51] and X ϭ Cl.…”
Section: Photolytic (Cisϫtrans) or Base-catalyzed (Prototropic) Isommentioning
confidence: 99%
“…21. In the case of compounds of type 30 with X ϶ H, the influence of X and the phenyl group at C-1 on the chemical shift of the 3-H signal is not as straightforward as might appear considering the compounds in Table 1. Thus, the configurations of compounds 30 cannot easily be correlated with the δ values of 3-H, as shown, for example, by considering the data for 30a with X ϭ Me, [46] X ϭ F, [47] X ϭ Scheme 6. NOE enhancements observed for the 1 H NMR signals Cl, [48] and X ϭ Br [49] or 30b with X ϭ Me, [50] X ϭ Bu, [9] of (E)-3 and results derived from 1 H NMR spectra of 4t and 26t X ϭ CH 2 Ph, [51] and X ϭ Cl.…”
Section: Photolytic (Cisϫtrans) or Base-catalyzed (Prototropic) Isommentioning
confidence: 99%